OnlyFans creator on the one X-rated act that left her in tears

Ruby Drew has opened up about navigating a healthy relationship while running her OnlyFans: including the lessons she’s learned the hard way.

For most, telling a potential partner what you do for work is a fairly mundane conversation but for Ruby, answering the dreaded career question on a first date with her now-partner, Jakob was daunting.

“It can be a pretty scary thing telling the guy you’re seeing that you have an OnlyFans. Because there’s a good chance they’ll respond horribly, and it’ll be the last time you see them,” Ruby says.

“When I started my OnlyFans, dating wasn’t my priority. I’d just come out of a pretty toxic relationship, where my partner hated what I did for work [stripping] and I started my account as soon as we broke up, in part due to a little bit of spite. I was loving focusing on myself and building my career when I met my now-boyfriend.”

Despite dating not being her focus at the time, Ruby found herself attracted to Jakob in just a few days, prompting her to open up to him.

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"Thankfully, he was very supportive. He found it cool that I had so much freedom to pursue my interests... He was just happy to see me happy."

Knowing how Ruby made money from the get-go, her boyfriend, Jakob, was happy to watch her create content with other women.

“Watching my videos [with other girls] back is like Christmas for him. I like girls as well, and when I told him it was something I’d like to explore more, he was like: ‘that’s hot as f***. You can explore that, no problem.’”

Threesome gone wrong

It didn't take long before Ruby decided to involve him in the act, with the couple experimenting with threesomes.

“We had a rule that he could only touch and penetrate me, but then, one night I was a bit tipsy and told him I was okay for him to have sex with the other girl,” Ruby said.

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“It’s really hard to know what you’re comfortable with until you’re in the moment. And the one time I decided to be the ‘cool girlfriend’ and let him have sex with another girl, I cried the whole next day.

“I was driving to the gym and I couldn’t get the image out of my mind. Yeah, so never again.”

Ruby says navigating any relationship with aspects of non-monogamy requires open conversation and plenty of trial and error.

“There are lots of things we’re comfortable with doing that might seem counterintuitive. We’ve been to sex clubs where we’re happy to be watched, but I can get jealous when he interacts with other girls. I’m okay with Jakob watching me have sex with other women, as long as he focuses on me while we’re doing it.”

Nowadays, Ruby employs her boyfriend full-time as her assistant – far from the unsupportive relationship that set her on the road to OnlyFans.

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